Trifluoroacetic acid → 4-(3-(1H-pyrazol-4-yl)pyridin-2-yloxy)benzenamine

HRID 227770Notes

Reaction equation

HRID 227770 reaction equation
C([N:20]1[CH:24]=[C:23]([C:25]2[C:26]([O:31][C:32]3[CH:37]=[CH:36][C:35]([NH2:38])=[CH:34][CH:33]=3)=[N:27][CH:28]=[CH:29][CH:30]=2)[CH:22]=[N:21]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.FC(F)(F)C(O)=O>CO>[NH:20]1[CH:24]=[C:23]([C:25]2[C:26]([O:31][C:32]3[CH:37]=[CH:36][C:35]([NH2:38])=[CH:34][CH:33]=3)=[N:27][CH:28]=[CH:29][CH:30]=2)[CH:22]=[N:21]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 667318804-(3-(1-trityl-1H-pyrazol-4-yl)pyridin-2-yloxy)benzenamine

Product 1

HCID 577562374-(3-(1H-pyrazol-4-yl)pyridin-2-yloxy)benzenamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

In a 25 mL sealed tube, was added 4-(3-(1-trityl-1H-pyrazol-4-yl)pyridin-2-yloxy)benzenamine (0.150 g, 0.303 mmol), trifluoroacetic acid (0.23 mL, 3.0 mmol), and methanol (1.0 mL). The mixture was stirred at 80° C. for 36 hours. The mixture was concentrated. The residue was extracted into EtOAc, washed 1×NaHCO3, 1×NaCl, and the organic layers were combined and dried over Mg2SO4, filtered through fritted funnel and concentrated to yield 4-(3-(1H-pyrazol-4-yl)pyridin-2-yloxy)benzenamine as dark brown waxy solid. MS m/z=253 [M+1]+. Calc'd for C14H12N4O: 252.27.

Workup

  1. customIn a 25 mL sealed tube
  2. concentrationThe mixture was concentrated
  3. extractionThe residue was extracted into EtOAc
  4. washwashed 1×NaHCO3, 1×NaCl
  5. dry with materialdried over Mg2SO4
  6. filtrationfiltered through fritted funnel
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b48f6e8839854561976f8c450c2c4734
Source dataset
uspto-grants-2009_07
Patent number
US07560551B2

Reaction notes

Loading…